I never really thought about what a disaster victory would bring. After all, not long after Neo is freed, Morpheus tells him:
“We have a rule. We never free a mind once it’s reached a certain age. It’s dangerous, the mind has trouble letting go.”
The very nature of the fictional universe is such that you really can’t try to figure it out. As it is, much of the movies have patchwork explanations to make it function. Why is combat in the Matrix potentially fatal? Uh, the body can’t live without the mind. So why not unplug a person who’s losing a fight? Uh… because! But you have to throw those things in or else the action scenes have no stakes. If opur heroes can stop a fight anytime things don’t go their way, the way you’d turn off an Xbox, there are no stakes, and there is no drama. Why can’t humans live in an utopian Matrix? That’s never really explained either, but if the Matrix doesn’t look like 1999 Earth it’s harder to film and harder to explain why anyone wouldn’t enjoy being in it.
This is one of the reasons why the original was great and the sequels not so much. Trying to dig into it isn’t wise.
I’ll definitely skip The Matrix Part 14: Billions of people yoinked out of the simulation, handed shovels and told to rebuild Zion. You’re free! Yay!
Guys, that never happened. This is what happens at the end of the first trilogy.
I guess I did miss something.
So billions stayed plugged in?
But that wouldn’t happen if those goddamned rebels would stop shooting up the place!
It is all pretty straightforward religious symbolism. Every single character has a Meaningful Name (Cipher = 0, Trinity, The One (Anderson, the Son of Man), Morpheus, Apoc, etc etc) And of course the body cannot live without a soul. Anyway, the Matrix = Maya (illusion; also the name of the Buddha’s mother), among other things. Surely someone has gone down this rabbit-hole 
and laid it all out for us.
Yes, without them the machines would die off. The peace was only about letting Zion live and freeing the very few people who didn’t buy into the matrix.
We don’t know. The third movie ends with the Architect telling the Oracle that those who want out will be freed. We’re not told how many of those there are.
All Neo negotiates for is “peace,” when asked by Deus Ex Machina. He just wants the war to end, for the Machines to stop attacking those who choose to leave the Matrix. If he was going for everyone being freed, I’d expect a word like “freedom.” (And even that could just mean the freedom to choose.)
As for your question in the OP: I would expect that it depends heavily on how good they had it. Even if we assume a modified 1999 (it seems very city-focused, with its placement of connections and such), the movies make it pretty clear that things are not perfect. So there will probably be people who are worse off inside than outside, even if they don’t care about being “freed.” One thing I notice is that racism doesn’t appear to be a thing in Zion.
That is not true of the 1990s boom era that the Matrix is modeled after.
To answer the OP, it was just fine for the overwhelming majority, but to some people it always felt wrong. I guess it was ok for anyone who bought in.